Blackmailed Into Submission

About six months ago I took on two roommates (a male and one female) because I was unable to meet my financial responsibilities. The roommate I will be referring to is a female, 23yr. old, 5’7,” thin with short reddish brown hair, an ass that won’t quit and muscular thighs that would make your insides tingle. I saw her sunbathing one day and about shot my load right there. She wasn’t as thin as I had first thought. But she had such a firm, toned body and those athletic thighs, and those perky breasts, just big enough to fit in my mouth, it drove me nuts. She must shave enough to hide the hair if not all the way because I couldn’t see any when I stood in front of her talking.

The house we lived in was being sold and I thought we would just go our separate ways. Then Jessica and I decided to continue being roommates and moved into another house together. It seemed the right thing to do and we both would be able to get out of debt.

All the while we were living together, in the first house, we both dated other people. We did exchange the fact that we both thought each other attractive, but we didn’t want to cross the line and ruin the roommate thing, so we never made any advances on each other. But sometimes you could feel the tension in the air. Especially after I got to know more through our conversations about her sexual habits.

I would be in my room next to hers and hear her ‘sport fucking’, as she would put it. I wasn’t into ‘sport fucking’, I wanted a relationship. But damn how I wish I could have been the one sporting her just once. Hearing her made me as horny as a 20 year old. I usually masturbated twice a day. I’m 36 and really wanted to take things slow and develop a relationship before the sex got too involved. I know, sounds like BS, but it is the truth. I was tired of the dating game and single life.

From the time I was about 13 and read an X rated newspaper about enemas, I have been giving myself enemas and have learned several ways to enhance masturbation with enemas. But even when I was married, my wife didn’t like them and didn’t want to satisfy my need for them either. So goes life.

Jessica and I moved into a nice house, our bedrooms were at the opposite ends of the hall way, at lease now I wouldn’t be driven crazy hearing her ‘sport fucking’. She had the master bedroom and bath, and the hall bath was mine.

Now when you have lived with someone for a while you get to know their habits, like when they go to work and when they come home. She never came home during the day, never, until one day…

I was home working and I got this urge to have an enema and an exquisite release of built up cum in my balls. So here I am bent over with my homemade enema nozzle up my ass, the bathroom door ajar just a little so I could hear if anyone came to the front door…she did come home…but I was so into what I was doing, I didn’t hear or pay any attention to anything.

As I was stroking my cock and the water was filling my insides, all of a sudden I heard this faint, “Hum…that looks interesting.”

OH SHIT, OH GOD, OH SHIT. (thinking to myself). I was caught as red handed as anyone could be. But she turned and left the house, back to work I assumed.

The rest of the day was horrible. So many things entered into my mind, like she probably thinks I’m so weird, she’ll want to move…etc. etc. The bills. How in the hell would I explain this ? Damn, damn, damn.

Well the time came when she was home from work, I started to explain but she held up her hand and said, “It’s your business, I sport fuck and you do what you do, to each their own.”

Oh what a relief, but I was still embarrassed.

After I was over the embarrassment, our conversations were back to the same old hum drum stuff. But I noticed she hadn‘t had anybody over since she caught me. Actually she hadn’t gone out either. In our conversations we would chit chat about the people we had been dating, so one night I asked her how her dating was going.

I opened up a can of worms right there. She told me that she hadn’t found anyone interesting lately.

“I’m sorry to hear that,” I replied.

She said, in a voice I had never heard before, “I’m tired of guys that don’t get me off and then leave me hanging.” I was shocked to hear that from her as I remembered the moans and groans I used to hear.

I started to tell her that was why I wanted to be in a relationship because sex isn’t everything, there has to be emotions involved and you need to know that the person wants to do all that they can to get you to your climax. I guess us guys get this way in our late 30’s.

Then she changed the subject and said, “What was that red thing I saw in your ass that day?”

Oh damn, I must have turned ten sheets of red. The red thing she was referring to was my homemade nozzle.

A long time ago I didn’t want to wait for the mail order to buy a inflatable nozzle, so I bought a butt plug about inch and a half in diameter and drilled a hole in the center to fit the regular small round nozzle that comes with the bags you buy in the store. I really had to take my time and get my ass ready for it or it hurt like hell. But once in, I could take all the water without worrying about leaking or about any messes when I would cum. It would press against my prostate glad and really enhance my orgasm.

I choked and said, “I don’t really talk about such intimate things unless I’m in a meaningful relationship with a person I feel comfortable talking to.” Thinking I had stifled that subject I said goodnight and started to walk away.

“But Jim, I really think you own me an explanation,” she said in a sort of demanding voice.

“I know,” I said.

“To each their own, but seeing you doing that has stuck in my mind. So tell me, what was it ?” she asked.

The pause and silence was like eternity. I could feel my face getting redder by the micro second. So I just blurted it out. “It was a nozzle for the enema. OK ? And goodnight.” Then I turned to walk away.

She stepped in front of me and said, “I’ve seen an enema bag and an enema nozzle before. Was that what you were using ? Show it to me.”

Damn, she wasn’t going to give up. Now most guys would have loved the idea of having this sexy 23 year old questioning them about their sexual practices and being asked to show off their toys, but I didn’t want to share something so personal with someone I only knew as a roommate.

In protest I said, “Sorry, I think not.”

But before I could protest any more she said, in an even more demanding voice, “You are going to do what I say and show me or everyone who knows you, including your office associates, will know what you do in private. Now, you are going to show me that or else ?”

I was had, I said OK and walked into my room.

With a smile that showed her victory, she said, “Oh this is going to be fun. Get all your stuff and meet me in my bathroom.” I only brought out the simple fun things I liked : Epson salt, lubricant and the nozzle.

In her bathroom, she asked me to describe the things she saw. I explained what each one did, salt, lubricant, and how the small white nozzle fit into the red homemade butt plug/nozzle. I told her about the temperature of the water, etc. Damn, the look on her face was almost evil. I was getting nervous.

She said, “You’re holding out on me, I smelled the peppermint and saw the label on the castile soap, where is it?” Great, a chic who doesn’t even know about enemas and wants to know where the soap is (I’m thinking).

In an educated voice she said, “I used to play doctor when I was a little girl and in college I took one semester of medical assistant care, so don’t hold out on me again or the water will be cold. Do you have a thermometer? Never mind. I have one, go get the soap.”

When I returned she had spread a towel on the floor and told me to strip. I had never felt so humiliated in my life. She just looked at me and said, “Don’t even think of refusing. Now get your clothes off, I’m giving you an enema with your own special nozzle.” The tone in her voice was demanding but now almost tauntingly evil too.

“All right, but you have to be very careful. The last time I did this was when you caught me three weeks ago and you will have to be careful not to hurt me with that nozzle.” (Sometimes I even hurt myself by accident it feels so big).

She just looked at me and said, “Look, if you haven’t figured it out yet, I’m in control here, all you have to do is what you are told and I’ll do the rest, so strip and lay face down on the towel.” There was definitely no way of getting out of this, so I undressed and lay down on the towel.

Here I lay in front of this sexy 23 year old chic, whom I wish I was the one giving her the enema. I was ass-naked and exposed to her completely, and had no say in anything. I was completely at her mercy. I could have died right there.

As she prepared the bag with warm water and soap, she started talking to me saying, “Now Jim, I know you are very afraid of me doing this but just relax. You may not know this, but I do know what I’m doing. I had the opportunity to witness first hand how to give a rectal exam using an anoscope and of course us women get vaginal exams once a year. My last doctor was very gentle to me and I remember how nice he was compared to some of the fingers I’ve had up inside me. So you just put your fears to rest and relax. If I start to hurt you, you tell me and I’ll go softer.”

The tone in her voice had changed to consoling and re-assuring. Thinking she might be softening up, I said, “We could always just not do this.”

With that she reached over with her small hand and gave my bare ass a slap, “You stay right where you are and that’s final,” again in that stern voice. “For that you will pay, you’ll see.”

The slap caused a little tingle that radiated to my balls, my penis contracted too. The bag was full and bulging with hot soapy water. She positioned herself between my legs and told me to spread them so she could sit down. Now there was no hiding my manhood at all. Completely exposed, my dick was peeking out underneath my balls. She had the entire view. How vulnerable I was.

I’ve had female doctors check for hernia’s and not been so humiliated. She started to touch my ass cheek, with almost kind, soft hands, rubbing and kneading them, one in each hand. This really didn’t feel so bad after all. Hum…actually this felt great. My mind started to wander. The sensation of her little firm hands touching me was really making me succumb to her will.

Before I realized what was happening, I felt something push against my anus and I tensed up. She said, “Jim, I’m going to take your temperature and I need put lube in you with my finger, just take a deep breath and relax.” Only doctors for medical reasons have been the ones to put anything back there in my entire life. Now to have someone I’m not close to or haven’t been sexually intimate with doing this to me. You would jump too.

She spread my cheeks with one hand and with the other started pushing her petite finger into me. In a playful voice she said, “Oh yeah, let it go in real nice and s l o w.” Then she started twisting her finger inside me, pressing on my prostate. The sensations : Oh wow, this was really not so bad and it was starting to feel exquisite, the tingles going through me, as her other hand began to massage my ass checks again. My mind began to wander, almost as though I had drank several gin and tonics.

Then without warning she inserted the thermometer into my asshole. She pulled it in and out, with a twisting motion at the same time.

It was cold and I jumped a little but she put her hand on the small of my back to hold me in place. Then she said in her sexy whispering voice, “Do you like this Jim ? Tell me how you feel, come on I know you’re enjoy this, I can tell cause your dick is getting bigger.”

She was right. I replied in a nervous yet panting voice, “This, this, is, umm yes this feels ok.”

Then after she had a reading she withdrew it from my asshole. “You’re normal.” Then she said, “I need to see how far I can go and if there is any blockage in there.” She slide her finger inside, just a little to start, then deeper and deeper, she went in so far, I could feel her finger like it was in my stomach. I didn’t know that she could get her finger in as deep as she did. Then she said, “We have to open you up to fit this nozzle inside.” With that, she slide her second finger in and continued to move them in and out. It felt so tight in there even though she was being very soft and gentle. She was being more gentle than I was when I did it. So sensual and soft, in and out. She was fucking my ass with her fingers.

While she kept a steady motion she said, “Jim, I’m glad you decided to do what I said, I’ll make sure you are well taken care of. Are you ready for the nozzle?”

“Oh not yet,” I replied in a moaning voice.

“Then we have to stretch you out a little.” With that she began to pull her fingers apart stretching me inside. Oh the pressure.

“Ouch, you’re spreading them too much,” I complained.

“Just take deep breathes and relax, we need to get you opened up further for your nozzle.” She continued, a few strokes more, then she inserted her other two fingers. Now the tight feeling was really noticeable. But the feeling of all her fingers in me was awesome, she was even moving them all around inside me as to massage the walls of my rectum.

Oh, the pressure of all four of her fingers was so much, I didn’t think the nozzle was even that big. “Do you like it when I put pressure on your prostate? By the looks of the pre-cum, I think you do.” Again she was right. I almost came but she must have sensed I was close so she pulled her fingers out as she finished talking. What a tease.

Then in a taunting voice, she said, “Here comes Big Red. Are you ready ?” By now my asshole was tingling so much I didn’t think I would feel it. But as she pushed it against my hole, I did feel every bit of it. In fact it started to sting a little, it was feeling hot. It made me squirm it felt so hot. At first I thought it was just because she spent so much time back there, but then she said, “Jim, meet my friend Vicks,”. Oh shit, that little girl did a surprise, I would have never guessed she would do that.

“Oh Jessica, you’re so tricky,” I complained.

She said, “I know, just a little something to remind you I can be tough if you forget who’s in control here.” And then she slid the nozzle inside me with one smooth push.

“Oh Jessica, oh god,” I gasp. The tightness. I felt a little pain but not enough to complain. Actually for this being the first time someone else was doing this to me, it felt good. Once it was completely inside me she began to move it around, pushing against my prostate. She moved it in and out so gently. By now the Vicks had stopped burning but the coolness was still there. The bulb of the butt plug expanded my hole as she pulled it out and pushed it in. This was really driving me into a state of excitement I had never imagined possible.

Then on the last push inward she stropped and said, “Get up on your knees, I want your dick to hang.” She grabbed hold of it and started to stoke me. She must have lubed her hand because it felt like satin against my cock.

“Is this how you do it ?” By now I really didn’t care what was going on, the sensations radiating through me was more than I could have ever dreamed of. I almost shot cum right there, but again she stopped everything, sensing I was close.

She said, “You’re not going to come until I do and if you do I’ll really fill you up hard. Roll over on your back,” she commanded. “Now lay still, I’m going to start the water flow.” She unclipped it just enough for the water to flow slowly into my insides. “Is that the right flow ?” she asked.

I just nodded yes. “Good, now you can take care of me while this is doing its thing.”

It didn’t really register what she said at first, because the warmth of the water that was filling me slowly caused my mind to become foggy. But then she got up and set her ass in my face and I saw her sweet little ass and shaved pussy. All I could do was lay there stunned. Then she told me to stick out my tongue. She lowered her ass onto my face, then moved around as if to work my tongue in and out of her ass hole. “Lick it, stick your tongue in my ass and lick it good.”

Oh the awesome smell of her sweet ass and the wetness that had accumulated around those sweet vaginal lips. Then she placed my hands on her breasts and motioned for me to pinch them gently. Oh gosh, the water flowing inside me began build its pressure and the soap started its slight cramping in my abdomen. I told her I was beginning to cramp but she just replied. “Keep licking my ass.”

I continued darting my tongue in and out of her tight little asshole. Jessica started moving more vigorously, then she moved backwards and slid her vaginal lips and clit in reach of my mouth, laying her body on top of mine. She took my throbbing member into her hand and started a firm rhythmic motion up and down.

The taste and aromas of her sweet sex was building my excitement, but now the cramps from the soap were getting worse. But because of all these other awesome sensations, this was like a sweet mild pain, unlike I have felt before. Was it because she didn’t put as much soap or was it just because so many good feelings were running through me right now ? Who cares. Oh god this was so exquisite.

I noticed her body was trembling and her moans became more rapid, her hips moved so firmly over my mouth, I had her love bud between my lips and my finger inserted into her little ass opening, gently moving in and out. With my other hand I had a firm grip on her, holding her tightly against my mouth.

Her keen senses realized that I was close too. She moaned, “Jim, I’m going to come so let yours go with me.”

I told her to go a head and I would wait so I could concentrate on her first. “OK I’m going to come. Oh here it comes, eat me. Yeah suck it harder now. Oh yes , ohhhh yyyeessss oooohhhhuuuu yyyyeessss.”

She exploded so hard that she squirt her love juice all over my face. The excess that I couldn’t catch in my mouth and swallow ran down my neck onto the floor. Awesome sweet sex juice from her quivering pussy. What a grand reward for eating her so good.

Then, just as she was coming to the end of her orgasm, she lowed her head and engulfed my cock into her little wet mouth. I wasn’t ready for that and didn’t expect it either. I thought she would just use her hand as she had been doing. But just as quick as she did that, she also let the flow in the bag go full force, her sweet mouth stoking me up and down with such a firm and steady motion, the water flow rushing past my glad insides. “Oh my, oh god, Oh JJJ EEE SSSS IIIII CCCC AAAA, oh yyyeeeessss….”

I shot so hard I thought she would take her head away. But she kept sucking and sucking. I thought she would never stop. She milked me so dry I thought my cock would never be the same. I never had someone do that so thoroughly. I don’t think I have ever cum that hard in all the years I’ve masturbated or with someone else.

Our bodies still trembling from the force of our orgasms, we just lay there, spent and out of energy to do anything but wallow in our sex. What a sight to see with her beautiful globes in my face and sweet juice glazed on my face. The scent of sex had the most intoxicating effect on me. Besides the fact that I had just received my first enema from her.

Finally I did have to expel the water. After cleaning up we lay on her bed just looked at each other, complimenting each other on such a wonderful night and talking about our possible future together. We were both in awe that after all the time that had past and all the other people we had dated, that we didn’t have this little sporting event sooner.

She was happy that for the first time, she came from having her clit eaten so good. Before we fell asleep she said, “Now, do I have to blackmail you into showing me how that water feels inside my little ass next time or will you just return the favor?”

I was happy to finally have an enemate. Who could have known that blackmail could turn out to be so much fun and a sporting event turn into a future relationship ?

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